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Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one

The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C(22)H(17)NO(2), (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C(14)H(17)NO(2), (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent m...

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Autores principales: Syed Abuthahir, S., NizamMohideen, M., Mayakrishnan, S., Uma Maheswari, N., Viswanathan, V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6690470/
https://www.ncbi.nlm.nih.gov/pubmed/31417776
http://dx.doi.org/10.1107/S2056989019009435
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author Syed Abuthahir, S.
NizamMohideen, M.
Mayakrishnan, S.
Uma Maheswari, N.
Viswanathan, V.
author_facet Syed Abuthahir, S.
NizamMohideen, M.
Mayakrishnan, S.
Uma Maheswari, N.
Viswanathan, V.
author_sort Syed Abuthahir, S.
collection PubMed
description The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C(22)H(17)NO(2), (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C(14)H(17)NO(2), (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. In I, the two phenyl rings are inclined to each other by 56.41 (7)° and to the mean plane of the 1H-isochromene ring system by 67.64 (6) and 44.92 (6)°. In both compounds, there is an intra­molecular N—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal of I, mol­ecules are linked by N—H⋯π inter­actions, forming chains along the b-axis direction. A C—H⋯π inter­action links the chains to form layers parallel to (100). The layers are then linked by a second C—H⋯π inter­action, forming a three-dimensional structure. In the crystal of II, the two independent mol­ecules (A and B) are linked by N—H⋯O hydrogen bonds, forming –A–B–A–B– chains along the [101] direction. The chains are linked into ribbons by C—H⋯π inter­actions involving inversion-related A mol­ecules. The latter are linked by offset π–π inter­actions [inter­centroid distances vary from 3.506 (1) to 3.870 (2) Å], forming a three-dimensional structure.
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spelling pubmed-66904702019-08-15 Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one Syed Abuthahir, S. NizamMohideen, M. Mayakrishnan, S. Uma Maheswari, N. Viswanathan, V. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C(22)H(17)NO(2), (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C(14)H(17)NO(2), (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. In I, the two phenyl rings are inclined to each other by 56.41 (7)° and to the mean plane of the 1H-isochromene ring system by 67.64 (6) and 44.92 (6)°. In both compounds, there is an intra­molecular N—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal of I, mol­ecules are linked by N—H⋯π inter­actions, forming chains along the b-axis direction. A C—H⋯π inter­action links the chains to form layers parallel to (100). The layers are then linked by a second C—H⋯π inter­action, forming a three-dimensional structure. In the crystal of II, the two independent mol­ecules (A and B) are linked by N—H⋯O hydrogen bonds, forming –A–B–A–B– chains along the [101] direction. The chains are linked into ribbons by C—H⋯π inter­actions involving inversion-related A mol­ecules. The latter are linked by offset π–π inter­actions [inter­centroid distances vary from 3.506 (1) to 3.870 (2) Å], forming a three-dimensional structure. International Union of Crystallography 2019-07-09 /pmc/articles/PMC6690470/ /pubmed/31417776 http://dx.doi.org/10.1107/S2056989019009435 Text en © Syed Abuthahir et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Syed Abuthahir, S.
NizamMohideen, M.
Mayakrishnan, S.
Uma Maheswari, N.
Viswanathan, V.
Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one
title Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one
title_full Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one
title_fullStr Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one
title_full_unstemmed Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one
title_short Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one
title_sort crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1h-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1h-isochromen-1-one
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6690470/
https://www.ncbi.nlm.nih.gov/pubmed/31417776
http://dx.doi.org/10.1107/S2056989019009435
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